Ethanol → HCID 77231187, compound

HRID 1696007Notes

Reaction equation

HRID 1696007 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][C@@H:10]([CH3:15])[C@@H:9]1[C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:23][CH2:24]O>>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][C@@H:10]([CH3:15])[C@@H:9]1[C:16]([O:18][CH2:23][CH3:24])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 67268470HCID 67268470, compound

Product 1

HCID 77231187HCID 77231187, compoundYield 61.4%

Conditions

Temperature
20 °C

Procedure

A round-bottomed flask equipped with a magnetic stirrer was added (2S,3R)-4-benzyl-2-methyl-5-oxomorpholine-3-carboxylic acid (1 g, 4.01 mmol), EtOH (20 ml), thionyl chloride (1.155 ml, 16.05 mmol). The reaction was stirred at 20° C. for 72 hours. Concentrate in vacuo to afford a crude oil. The oil was purified by silica gel column chromatography (eluting with 20% EtOAc in Hexanes using the Moritex SI-60 size 60—half column). The resultant fractions were collected and concentrated in-vacuo to afford (2S,3R)-ethyl 4-benzyl-2-methyl-5-oxomorpholine-3-carboxylate (683 mg, 2.46 mmol, 61.4% yield) as a white solid. MS [M+H] found 278.

Workup

  1. customA round-bottomed flask equipped with a magnetic stirrer
  2. concentrationConcentrate in vacuo
  3. customto afford a crude oil
  4. customThe oil was purified by silica gel column chromatography (
  5. washeluting with 20% EtOAc in Hexanes using the Moritex SI-60 size 60—half column)
  6. customThe resultant fractions were collected
  7. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-cdeecfc4e8e3461c852dcbb4a2047e12
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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